JPH03169840A - メラトニン作用物質及び拮抗物質としての置換２‐アミドテトラリン - Google Patents
メラトニン作用物質及び拮抗物質としての置換２‐アミドテトラリンInfo
- Publication number
- JPH03169840A JPH03169840A JP2254980A JP25498090A JPH03169840A JP H03169840 A JPH03169840 A JP H03169840A JP 2254980 A JP2254980 A JP 2254980A JP 25498090 A JP25498090 A JP 25498090A JP H03169840 A JPH03169840 A JP H03169840A
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- aryl
- tetralin
- hydrogen
- alkylaryl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- DRLFMBDRBRZALE-UHFFFAOYSA-N melatonin Chemical compound COC1=CC=C2NC=C(CCNC(C)=O)C2=C1 DRLFMBDRBRZALE-UHFFFAOYSA-N 0.000 title claims abstract description 128
- YJPIGAIKUZMOQA-UHFFFAOYSA-N Melatonin Natural products COC1=CC=C2N(C(C)=O)C=C(CCN)C2=C1 YJPIGAIKUZMOQA-UHFFFAOYSA-N 0.000 title claims abstract description 127
- 229960003987 melatonin Drugs 0.000 title claims abstract description 127
- 239000000126 substance Substances 0.000 title claims description 10
- 230000003042 antagnostic effect Effects 0.000 title description 7
- 230000009471 action Effects 0.000 title description 6
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 58
- 125000003118 aryl group Chemical group 0.000 claims abstract description 49
- 230000000694 effects Effects 0.000 claims abstract description 41
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 39
- 150000002367 halogens Chemical class 0.000 claims abstract description 39
- 125000002877 alkyl aryl group Chemical group 0.000 claims abstract description 38
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 35
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 20
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 19
- 125000004171 alkoxy aryl group Chemical group 0.000 claims abstract description 18
- 125000000304 alkynyl group Chemical group 0.000 claims abstract description 18
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 15
- 208000035475 disorder Diseases 0.000 claims abstract description 15
- 125000003368 amide group Chemical group 0.000 claims abstract description 12
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 10
- 125000004043 oxo group Chemical group O=* 0.000 claims abstract description 10
- 150000001875 compounds Chemical class 0.000 claims description 116
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Substances C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 claims description 83
- 238000000034 method Methods 0.000 claims description 50
- 229910052739 hydrogen Inorganic materials 0.000 claims description 46
- 239000001257 hydrogen Substances 0.000 claims description 46
- 150000002431 hydrogen Chemical class 0.000 claims description 40
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 27
- -1 2-chloroacetamide-tetralin Chemical compound 0.000 claims description 19
- 102000001419 Melatonin receptor Human genes 0.000 claims description 19
- 108050009605 Melatonin receptor Proteins 0.000 claims description 19
- 239000000203 mixture Substances 0.000 claims description 18
- 239000005557 antagonist Substances 0.000 claims description 17
- 125000003282 alkyl amino group Chemical group 0.000 claims description 15
- 239000000556 agonist Substances 0.000 claims description 14
- 125000001188 haloalkyl group Chemical group 0.000 claims description 9
- 239000008194 pharmaceutical composition Substances 0.000 claims description 9
- 230000002159 abnormal effect Effects 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 230000037396 body weight Effects 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
- 230000002401 inhibitory effect Effects 0.000 claims description 4
- 239000003550 marker Substances 0.000 claims description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 3
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 2
- PWLJBEDASDILHU-UHFFFAOYSA-N n-(4-benzyl-1,2,3,4-tetrahydronaphthalen-2-yl)acetamide Chemical compound C12=CC=CC=C2CC(NC(=O)C)CC1CC1=CC=CC=C1 PWLJBEDASDILHU-UHFFFAOYSA-N 0.000 claims description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims 7
- 239000004480 active ingredient Substances 0.000 claims 2
- 239000002671 adjuvant Substances 0.000 claims 1
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- RVIGBTUDFAGRTQ-UHFFFAOYSA-N N-(8-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)propanamide Chemical compound C1=CC(OC)=C2CC(NC(=O)CC)CCC2=C1 RVIGBTUDFAGRTQ-UHFFFAOYSA-N 0.000 abstract description 5
- 239000003814 drug Substances 0.000 abstract description 5
- 230000028327 secretion Effects 0.000 abstract description 5
- 208000010412 Glaucoma Diseases 0.000 abstract description 3
- 208000024891 symptom Diseases 0.000 abstract description 3
- 206010020772 Hypertension Diseases 0.000 abstract description 2
- 229940079593 drug Drugs 0.000 abstract description 2
- 208000020401 Depressive disease Diseases 0.000 abstract 1
- 239000000370 acceptor Substances 0.000 abstract 1
- 230000007547 defect Effects 0.000 abstract 1
- 238000001514 detection method Methods 0.000 abstract 1
- 208000024714 major depressive disease Diseases 0.000 abstract 1
- 201000003995 melancholia Diseases 0.000 abstract 1
- 238000012360 testing method Methods 0.000 description 34
- 238000000451 chemical ionisation Methods 0.000 description 29
- 239000007789 gas Substances 0.000 description 29
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 27
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 25
- VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 description 25
- 210000001525 retina Anatomy 0.000 description 23
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 21
- 239000000243 solution Substances 0.000 description 21
- 230000005764 inhibitory process Effects 0.000 description 19
- 230000006870 function Effects 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- FJDDSMSDZHURBJ-UHFFFAOYSA-N N-[2-(2-iodo-5-methoxy-1H-indol-3-yl)ethyl]acetamide Chemical compound COC1=CC=C2NC(I)=C(CCNC(C)=O)C2=C1 FJDDSMSDZHURBJ-UHFFFAOYSA-N 0.000 description 15
- 230000027455 binding Effects 0.000 description 15
- 241000283973 Oryctolagus cuniculus Species 0.000 description 13
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 11
- 239000011575 calcium Substances 0.000 description 11
- 229910052791 calcium Inorganic materials 0.000 description 11
- 230000027288 circadian rhythm Effects 0.000 description 11
- 230000001419 dependent effect Effects 0.000 description 11
- 230000002829 reductive effect Effects 0.000 description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- 229960003638 dopamine Drugs 0.000 description 10
- 230000033001 locomotion Effects 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 229940123784 Melatonin receptor antagonist Drugs 0.000 description 9
- 238000003556 assay Methods 0.000 description 9
- 238000002474 experimental method Methods 0.000 description 9
- VDJCYVYVTWEIPD-UHFFFAOYSA-N n-(8-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)acetamide Chemical compound C1CC(NC(C)=O)CC2=C1C=CC=C2OC VDJCYVYVTWEIPD-UHFFFAOYSA-N 0.000 description 9
- 230000002207 retinal effect Effects 0.000 description 9
- 230000000638 stimulation Effects 0.000 description 9
- 210000001519 tissue Anatomy 0.000 description 9
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
- 230000033228 biological regulation Effects 0.000 description 8
- LCGFVWKNXLRFIF-UHFFFAOYSA-N 1,2,3,4-tetrahydronaphthalen-2-amine Chemical compound C1=CC=C2CC(N)CCC2=C1 LCGFVWKNXLRFIF-UHFFFAOYSA-N 0.000 description 7
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 7
- 229940088597 hormone Drugs 0.000 description 7
- 239000005556 hormone Substances 0.000 description 7
- 230000003278 mimic effect Effects 0.000 description 7
- RVKOHSCTEHZRRT-UHFFFAOYSA-N 8-methoxy-1,2,3,4-tetrahydronaphthalen-2-amine Chemical compound C1CC(N)CC2=C1C=CC=C2OC RVKOHSCTEHZRRT-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- QXKHYNVANLEOEG-UHFFFAOYSA-N Methoxsalen Chemical group C1=CC(=O)OC2=C1C=C1C=COC1=C2OC QXKHYNVANLEOEG-UHFFFAOYSA-N 0.000 description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 229910052799 carbon Inorganic materials 0.000 description 6
- 230000000144 pharmacologic effect Effects 0.000 description 6
- 229940080818 propionamide Drugs 0.000 description 6
- 241000124008 Mammalia Species 0.000 description 5
- 241001465754 Metazoa Species 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 206010016256 fatigue Diseases 0.000 description 5
- 239000010410 layer Substances 0.000 description 5
- YNMJUMQDPHRKTA-UHFFFAOYSA-N n-(4-phenyl-1,2,3,4-tetrahydronaphthalen-2-yl)acetamide Chemical compound C12=CC=CC=C2CC(NC(=O)C)CC1C1=CC=CC=C1 YNMJUMQDPHRKTA-UHFFFAOYSA-N 0.000 description 5
- 239000012044 organic layer Substances 0.000 description 5
- 210000004560 pineal gland Anatomy 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 230000001850 reproductive effect Effects 0.000 description 5
- 239000000523 sample Substances 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- SLQUITRGZWAZBX-UHFFFAOYSA-N 2-chloro-n-(1,2,3,4-tetrahydronaphthalen-1-yl)acetamide Chemical compound C1=CC=C2C(NC(=O)CCl)CCCC2=C1 SLQUITRGZWAZBX-UHFFFAOYSA-N 0.000 description 4
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 4
- UCTMLZBVNPSJHC-UHFFFAOYSA-N 5-(2-aminoethyl)cyclohexa-2,4-diene-1,2-diol Chemical compound NCCC1=CC=C(O)C(O)C1 UCTMLZBVNPSJHC-UHFFFAOYSA-N 0.000 description 4
- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- WVVXBPKOIZGVNS-UHFFFAOYSA-N N-[2-[2-(phenylmethyl)-1H-indol-3-yl]ethyl]acetamide Chemical compound N1C2=CC=CC=C2C(CCNC(=O)C)=C1CC1=CC=CC=C1 WVVXBPKOIZGVNS-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- YZCKVEUIGOORGS-NJFSPNSNSA-N Tritium Chemical compound [3H] YZCKVEUIGOORGS-NJFSPNSNSA-N 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 230000003509 anti-fertility effect Effects 0.000 description 4
- 230000002860 competitive effect Effects 0.000 description 4
- 230000005684 electric field Effects 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 4
- 235000019341 magnesium sulphate Nutrition 0.000 description 4
- 208000015706 neuroendocrine disease Diseases 0.000 description 4
- 150000002923 oximes Chemical class 0.000 description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
- 230000003389 potentiating effect Effects 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- 230000001105 regulatory effect Effects 0.000 description 4
- 230000033764 rhythmic process Effects 0.000 description 4
- 208000012672 seasonal affective disease Diseases 0.000 description 4
- 210000003491 skin Anatomy 0.000 description 4
- 239000001632 sodium acetate Substances 0.000 description 4
- 235000017281 sodium acetate Nutrition 0.000 description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
- 229910052722 tritium Inorganic materials 0.000 description 4
- XGAFNQNJGUJDIN-UHFFFAOYSA-N 2-chloro-n-(4-phenyl-1,2,3,4-tetrahydronaphthalen-1-yl)acetamide Chemical compound C12=CC=CC=C2C(NC(=O)CCl)CCC1C1=CC=CC=C1 XGAFNQNJGUJDIN-UHFFFAOYSA-N 0.000 description 3
- ZPTITOXHTKKBPT-UHFFFAOYSA-N 4-phenyl-1,2,3,4-tetrahydronaphthalen-2-amine Chemical compound C12=CC=CC=C2CC(N)CC1C1=CC=CC=C1 ZPTITOXHTKKBPT-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
- WTDRDQBEARUVNC-LURJTMIESA-N L-DOPA Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-LURJTMIESA-N 0.000 description 3
- LUINDDOUWHRIPW-UHFFFAOYSA-N N-[2-(6-chloro-5-methoxy-1H-indol-3-yl)ethyl]acetamide Chemical compound C1=C(Cl)C(OC)=CC2=C1NC=C2CCNC(C)=O LUINDDOUWHRIPW-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 208000034972 Sudden Infant Death Diseases 0.000 description 3
- 206010042440 Sudden infant death syndrome Diseases 0.000 description 3
- 241000251539 Vertebrata <Metazoa> Species 0.000 description 3
- 150000008064 anhydrides Chemical class 0.000 description 3
- 230000003466 anti-cipated effect Effects 0.000 description 3
- 230000000903 blocking effect Effects 0.000 description 3
- 239000000872 buffer Substances 0.000 description 3
- 238000010531 catalytic reduction reaction Methods 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 230000002060 circadian Effects 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 238000000338 in vitro Methods 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- PNWBJKFDGPMHPB-UHFFFAOYSA-N n-(1,2,3,4-tetrahydronaphthalen-2-yl)acetamide Chemical compound C1=CC=C2CC(NC(=O)C)CCC2=C1 PNWBJKFDGPMHPB-UHFFFAOYSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 230000000955 neuroendocrine Effects 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 3
- 230000002285 radioactive effect Effects 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 208000019116 sleep disease Diseases 0.000 description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
- 230000002269 spontaneous effect Effects 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- 210000000221 suprachiasmatic nucleus Anatomy 0.000 description 3
- 229940124597 therapeutic agent Drugs 0.000 description 3
- 230000001225 therapeutic effect Effects 0.000 description 3
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical class CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 2
- QKNYBSVHEMOAJP-UHFFFAOYSA-N 2-amino-2-(hydroxymethyl)propane-1,3-diol;hydron;chloride Chemical compound Cl.OCC(N)(CO)CO QKNYBSVHEMOAJP-UHFFFAOYSA-N 0.000 description 2
- VMZCDNSFRSVYKQ-UHFFFAOYSA-N 2-phenylacetyl chloride Chemical compound ClC(=O)CC1=CC=CC=C1 VMZCDNSFRSVYKQ-UHFFFAOYSA-N 0.000 description 2
- KCKZIWSINLBROE-UHFFFAOYSA-N 3,4-dihydro-1h-naphthalen-2-one Chemical class C1=CC=C2CC(=O)CCC2=C1 KCKZIWSINLBROE-UHFFFAOYSA-N 0.000 description 2
- JJMVSSDNVDLCSV-UHFFFAOYSA-N 4-benzyl-3,4-dihydro-2h-naphthalen-1-one Chemical compound C12=CC=CC=C2C(=O)CCC1CC1=CC=CC=C1 JJMVSSDNVDLCSV-UHFFFAOYSA-N 0.000 description 2
- 208000007848 Alcoholism Diseases 0.000 description 2
- 208000019901 Anxiety disease Diseases 0.000 description 2
- 102000007527 Autoreceptors Human genes 0.000 description 2
- 108010071131 Autoreceptors Proteins 0.000 description 2
- 241000271566 Aves Species 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- 208000019888 Circadian rhythm sleep disease Diseases 0.000 description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
- WTDRDQBEARUVNC-UHFFFAOYSA-N L-Dopa Natural products OC(=O)C(N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-UHFFFAOYSA-N 0.000 description 2
- 206010024264 Lethargy Diseases 0.000 description 2
- 208000019022 Mood disease Diseases 0.000 description 2
- NVUGEQAEQJTCIX-UHFFFAOYSA-N N-acetyltryptamine Chemical compound C1=CC=C2C(CCNC(=O)C)=CNC2=C1 NVUGEQAEQJTCIX-UHFFFAOYSA-N 0.000 description 2
- FZRKAZHKEDOPNN-UHFFFAOYSA-N Nitric oxide anion Chemical compound O=[N-] FZRKAZHKEDOPNN-UHFFFAOYSA-N 0.000 description 2
- 208000008469 Peptic Ulcer Diseases 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- 206010036618 Premenstrual syndrome Diseases 0.000 description 2
- 201000001880 Sexual dysfunction Diseases 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 206010044565 Tremor Diseases 0.000 description 2
- 150000008065 acid anhydrides Chemical class 0.000 description 2
- 230000003213 activating effect Effects 0.000 description 2
- 201000007930 alcohol dependence Diseases 0.000 description 2
- 230000036506 anxiety Effects 0.000 description 2
- YHASWHZGWUONAO-UHFFFAOYSA-N butanoyl butanoate Chemical compound CCCC(=O)OC(=O)CCC YHASWHZGWUONAO-UHFFFAOYSA-N 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 210000004027 cell Anatomy 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 108010011222 cyclo(Arg-Pro) Proteins 0.000 description 2
- 230000003111 delayed effect Effects 0.000 description 2
- 206010015037 epilepsy Diseases 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- 239000012458 free base Substances 0.000 description 2
- 238000007429 general method Methods 0.000 description 2
- 238000005984 hydrogenation reaction Methods 0.000 description 2
- 229940053999 hypnotics and sedatives melatonin receptor agonists Drugs 0.000 description 2
- 201000001881 impotence Diseases 0.000 description 2
- 238000011534 incubation Methods 0.000 description 2
- 208000000509 infertility Diseases 0.000 description 2
- 230000036512 infertility Effects 0.000 description 2
- 231100000535 infertility Toxicity 0.000 description 2
- 230000004410 intraocular pressure Effects 0.000 description 2
- 239000003446 ligand Substances 0.000 description 2
- 210000003442 median eminence Anatomy 0.000 description 2
- 230000001404 mediated effect Effects 0.000 description 2
- 239000012528 membrane Substances 0.000 description 2
- 230000004060 metabolic process Effects 0.000 description 2
- YLSJLYYBVHQMEQ-UHFFFAOYSA-N n-(7-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)acetamide Chemical compound C1CC(NC(C)=O)CC2=CC(OC)=CC=C21 YLSJLYYBVHQMEQ-UHFFFAOYSA-N 0.000 description 2
- 239000002858 neurotransmitter agent Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 239000011574 phosphorus Substances 0.000 description 2
- 108091008695 photoreceptors Proteins 0.000 description 2
- 230000001766 physiological effect Effects 0.000 description 2
- 230000001817 pituitary effect Effects 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 229910052697 platinum Inorganic materials 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 208000020016 psychiatric disease Diseases 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 239000002287 radioligand Substances 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 230000033458 reproduction Effects 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 230000004517 retinal physiology Effects 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 230000001932 seasonal effect Effects 0.000 description 2
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 2
- 231100000872 sexual dysfunction Toxicity 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 230000035882 stress Effects 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 239000003039 volatile agent Substances 0.000 description 2
- PNVPNXKRAUBJGW-UHFFFAOYSA-N (2-chloroacetyl) 2-chloroacetate Chemical compound ClCC(=O)OC(=O)CCl PNVPNXKRAUBJGW-UHFFFAOYSA-N 0.000 description 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
- JRZGPXSSNPTNMA-UHFFFAOYSA-N 1,2,3,4-tetrahydronaphthalen-1-amine Chemical compound C1=CC=C2C(N)CCCC2=C1 JRZGPXSSNPTNMA-UHFFFAOYSA-N 0.000 description 1
- XHLHPRDBBAGVEG-UHFFFAOYSA-N 1-tetralone Chemical class C1=CC=C2C(=O)CCCC2=C1 XHLHPRDBBAGVEG-UHFFFAOYSA-N 0.000 description 1
- IANAMYWOIYNFFT-UHFFFAOYSA-N 2-amino-4-benzyl-3,4-dihydro-2h-naphthalen-1-one Chemical compound C12=CC=CC=C2C(=O)C(N)CC1CC1=CC=CC=C1 IANAMYWOIYNFFT-UHFFFAOYSA-N 0.000 description 1
- IWZVPQCTRQSJHM-UHFFFAOYSA-N 2-chloro-n-(8-methoxy-1,2,3,4-tetrahydronaphthalen-1-yl)acetamide Chemical compound C1CCC(NC(=O)CCl)C2=C1C=CC=C2OC IWZVPQCTRQSJHM-UHFFFAOYSA-N 0.000 description 1
- DGMOBVGABMBZSB-UHFFFAOYSA-N 2-methylpropanoyl chloride Chemical compound CC(C)C(Cl)=O DGMOBVGABMBZSB-UHFFFAOYSA-N 0.000 description 1
- YEYOTOKXQGXGFL-UHFFFAOYSA-N 2-phenyl-n-(1,2,3,4-tetrahydronaphthalen-1-yl)acetamide Chemical compound C1CCC2=CC=CC=C2C1NC(=O)CC1=CC=CC=C1 YEYOTOKXQGXGFL-UHFFFAOYSA-N 0.000 description 1
- UMWCJVVBXKGDIV-UHFFFAOYSA-N 4-phenyl-3,4-dihydro-1h-naphthalen-2-one Chemical compound C12=CC=CC=C2CC(=O)CC1C1=CC=CC=C1 UMWCJVVBXKGDIV-UHFFFAOYSA-N 0.000 description 1
- DWAQDRSOVMLGRQ-UHFFFAOYSA-N 5-methoxyindole Chemical group COC1=CC=C2NC=CC2=C1 DWAQDRSOVMLGRQ-UHFFFAOYSA-N 0.000 description 1
- ZNWNWWLWFCCREO-UHFFFAOYSA-N 7-methoxy-1,2,3,4-tetrahydronaphthalen-2-amine Chemical compound C1CC(N)CC2=CC(OC)=CC=C21 ZNWNWWLWFCCREO-UHFFFAOYSA-N 0.000 description 1
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
- 208000024827 Alzheimer disease Diseases 0.000 description 1
- 108091003079 Bovine Serum Albumin Proteins 0.000 description 1
- 206010006187 Breast cancer Diseases 0.000 description 1
- 208000026310 Breast neoplasm Diseases 0.000 description 1
- 101000654316 Centruroides limpidus Beta-toxin Cll2 Proteins 0.000 description 1
- 241000699800 Cricetinae Species 0.000 description 1
- 241000938605 Crocodylia Species 0.000 description 1
- NPOJQCVWMSKXDN-UHFFFAOYSA-N Dacthal Chemical compound COC(=O)C1=C(Cl)C(Cl)=C(C(=O)OC)C(Cl)=C1Cl NPOJQCVWMSKXDN-UHFFFAOYSA-N 0.000 description 1
- 206010012289 Dementia Diseases 0.000 description 1
- 101100075747 Drosophila melanogaster Lztr1 gene Proteins 0.000 description 1
- 241000287828 Gallus gallus Species 0.000 description 1
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 1
- 241000238631 Hexapoda Species 0.000 description 1
- 208000001456 Jet Lag Syndrome Diseases 0.000 description 1
- 101800001751 Melanocyte-stimulating hormone alpha Proteins 0.000 description 1
- 230000010667 Melatonin Receptor Interactions Effects 0.000 description 1
- 229940121723 Melatonin receptor agonist Drugs 0.000 description 1
- 239000004677 Nylon Substances 0.000 description 1
- 208000027089 Parkinsonian disease Diseases 0.000 description 1
- 241001494479 Pecora Species 0.000 description 1
- 241001006154 Phara Species 0.000 description 1
- 208000007641 Pinealoma Diseases 0.000 description 1
- 229920002873 Polyethylenimine Polymers 0.000 description 1
- 102100027467 Pro-opiomelanocortin Human genes 0.000 description 1
- 241001474791 Proboscis Species 0.000 description 1
- 201000004681 Psoriasis Diseases 0.000 description 1
- 208000028017 Psychotic disease Diseases 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- AUYYCJSJGJYCDS-LBPRGKRZSA-N Thyrolar Chemical class IC1=CC(C[C@H](N)C(O)=O)=CC(I)=C1OC1=CC=C(O)C(I)=C1 AUYYCJSJGJYCDS-LBPRGKRZSA-N 0.000 description 1
- 150000001263 acyl chlorides Chemical class 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 150000001266 acyl halides Chemical class 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 238000004220 aggregation Methods 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 230000001270 agonistic effect Effects 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000008485 antagonism Effects 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 230000003376 axonal effect Effects 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- CHIHQLCVLOXUJW-UHFFFAOYSA-N benzoic anhydride Chemical compound C=1C=CC=CC=1C(=O)OC(=O)C1=CC=CC=C1 CHIHQLCVLOXUJW-UHFFFAOYSA-N 0.000 description 1
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
- 239000012888 bovine serum Substances 0.000 description 1
- 229940098773 bovine serum albumin Drugs 0.000 description 1
- 210000004556 brain Anatomy 0.000 description 1
- 230000003925 brain function Effects 0.000 description 1
- 239000007853 buffer solution Substances 0.000 description 1
- SPKOTSGPUVTJGB-UHFFFAOYSA-N butan-1-amine;1,2,3,4-tetrahydronaphthalene Chemical compound CCCCN.C1=CC=C2CCCCC2=C1 SPKOTSGPUVTJGB-UHFFFAOYSA-N 0.000 description 1
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000005907 cancer growth Effects 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000036978 cell physiology Effects 0.000 description 1
- 230000009134 cell regulation Effects 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 230000003280 chronobiological effect Effects 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 239000002178 crystalline material Substances 0.000 description 1
- 230000001186 cumulative effect Effects 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 238000006264 debenzylation reaction Methods 0.000 description 1
- 238000004042 decolorization Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 239000002027 dichloromethane extract Substances 0.000 description 1
- 230000003292 diminished effect Effects 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 230000008034 disappearance Effects 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 230000007368 endocrine function Effects 0.000 description 1
- 230000004795 endocrine process Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 210000000981 epithelium Anatomy 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 230000010006 flight Effects 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- 230000002710 gonadal effect Effects 0.000 description 1
- 230000003779 hair growth Effects 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 239000000960 hypophysis hormone Substances 0.000 description 1
- 230000002267 hypothalamic effect Effects 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 208000036260 idiopathic disease Diseases 0.000 description 1
- 150000002466 imines Chemical class 0.000 description 1
- 230000028993 immune response Effects 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
- 150000002475 indoles Chemical class 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 210000000936 intestine Anatomy 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 229940047889 isobutyramide Drugs 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 208000033915 jet lag type circadian rhythm sleep disease Diseases 0.000 description 1
- 208000037805 labour Diseases 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- 238000005567 liquid scintillation counting Methods 0.000 description 1
- 239000006193 liquid solution Substances 0.000 description 1
- 239000002075 main ingredient Substances 0.000 description 1
- 206010025482 malaise Diseases 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000035800 maturation Effects 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 210000002780 melanosome Anatomy 0.000 description 1
- QHWKKWSNAVSLFR-UHFFFAOYSA-N n-(4-benzyl-1,2,3,4-tetrahydronaphthalen-2-yl)propanamide Chemical compound C12=CC=CC=C2CC(NC(=O)CC)CC1CC1=CC=CC=C1 QHWKKWSNAVSLFR-UHFFFAOYSA-N 0.000 description 1
- NSSWGYCGVXGLEN-UHFFFAOYSA-N n-(4-benzyl-1-oxo-3,4-dihydro-2h-naphthalen-2-yl)acetamide Chemical compound C12=CC=CC=C2C(=O)C(NC(=O)C)CC1CC1=CC=CC=C1 NSSWGYCGVXGLEN-UHFFFAOYSA-N 0.000 description 1
- HVKVUHPYXTYWNH-UHFFFAOYSA-N n-(5-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)acetamide Chemical compound C1C(NC(C)=O)CCC2=C1C=CC=C2OC HVKVUHPYXTYWNH-UHFFFAOYSA-N 0.000 description 1
- WKLXZRORELVODO-UHFFFAOYSA-N n-(8-methoxy-4-phenyl-1,2,3,4-tetrahydronaphthalen-2-yl)acetamide Chemical compound C1C(NC(C)=O)CC=2C(OC)=CC=CC=2C1C1=CC=CC=C1 WKLXZRORELVODO-UHFFFAOYSA-N 0.000 description 1
- 230000001537 neural effect Effects 0.000 description 1
- 239000000712 neurohormone Substances 0.000 description 1
- 230000007658 neurological function Effects 0.000 description 1
- 230000003705 neurological process Effects 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 230000009871 nonspecific binding Effects 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000008520 organization Effects 0.000 description 1
- 230000002611 ovarian Effects 0.000 description 1
- 230000016087 ovulation Effects 0.000 description 1
- 230000027758 ovulation cycle Effects 0.000 description 1
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000004031 partial agonist Substances 0.000 description 1
- 230000036961 partial effect Effects 0.000 description 1
- 230000001575 pathological effect Effects 0.000 description 1
- 210000001539 phagocyte Anatomy 0.000 description 1
- 230000035790 physiological processes and functions Effects 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 208000024724 pineal body neoplasm Diseases 0.000 description 1
- 201000004123 pineal gland cancer Diseases 0.000 description 1
- 229910003446 platinum oxide Inorganic materials 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 238000011533 pre-incubation Methods 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 229940044601 receptor agonist Drugs 0.000 description 1
- 239000000018 receptor agonist Substances 0.000 description 1
- 229940044551 receptor antagonist Drugs 0.000 description 1
- 239000002464 receptor antagonist Substances 0.000 description 1
- 102000005962 receptors Human genes 0.000 description 1
- 108020003175 receptors Proteins 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 210000000964 retinal cone photoreceptor cell Anatomy 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229940076279 serotonin Drugs 0.000 description 1
- 230000035938 sexual maturation Effects 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 230000009870 specific binding Effects 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 229960004940 sulpiride Drugs 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 230000001360 synchronised effect Effects 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000005495 thyroid hormone Substances 0.000 description 1
- 229940036555 thyroid hormone Drugs 0.000 description 1
- 230000001256 tonic effect Effects 0.000 description 1
- 230000026683 transduction Effects 0.000 description 1
- 238000010361 transduction Methods 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 230000001960 triggered effect Effects 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- WHNFPRLDDSXQCL-UAZQEYIDSA-N α-msh Chemical compound C([C@@H](C(=O)N[C@@H](CO)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC=1NC=NC=1)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)NCC(=O)N[C@@H](CCCCN)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](C(C)C)C(N)=O)NC(=O)[C@H](CO)NC(C)=O)C1=CC=C(O)C=C1 WHNFPRLDDSXQCL-UAZQEYIDSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/57—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of rings other than six-membered aromatic rings
- C07C233/60—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of rings other than six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
- C07C235/40—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of rings other than six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
- A61P27/06—Antiglaucoma agents or miotics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/02—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
- C07C233/04—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with carbon atoms of carboxamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
- C07C233/06—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with carbon atoms of carboxamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a ring other than a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/16—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
- C07C233/23—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a ring other than a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/64—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings
- C07C233/65—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/64—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings
- C07C233/67—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
- C07C233/74—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a ring other than a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/02—Systems containing only non-condensed rings with a three-membered ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/04—One of the condensed rings being a six-membered aromatic ring
- C07C2602/10—One of the condensed rings being a six-membered aromatic ring the other ring being six-membered, e.g. tetraline
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Ophthalmology & Optometry (AREA)
- Psychiatry (AREA)
- Hospice & Palliative Care (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Indole Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US411675 | 1989-09-25 | ||
| US07/411,675 US5071875A (en) | 1989-09-25 | 1989-09-25 | Substituted 2-amidotetralins as melatonin agonists and antagonists |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH03169840A true JPH03169840A (ja) | 1991-07-23 |
Family
ID=23629870
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2254980A Pending JPH03169840A (ja) | 1989-09-25 | 1990-09-25 | メラトニン作用物質及び拮抗物質としての置換２‐アミドテトラリン |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US5071875A (fr) |
| EP (1) | EP0420064A3 (fr) |
| JP (1) | JPH03169840A (fr) |
| KR (1) | KR910006218A (fr) |
| AU (2) | AU642429B2 (fr) |
| CA (1) | CA2025958A1 (fr) |
| IE (1) | IE903430A1 (fr) |
| PT (1) | PT95417A (fr) |
| ZA (1) | ZA907597B (fr) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2008518003A (ja) * | 2004-10-29 | 2008-05-29 | アストラゼネカ・アクチエボラーグ | 医薬品としての不飽和キノリンもしくはナフタレン誘導体の使用 |
| JP2009527462A (ja) * | 2006-01-06 | 2009-07-30 | セプラコア インコーポレーテッド | テトラロン系モノアミン再取り込み阻害剤 |
| JP2010518129A (ja) * | 2007-02-15 | 2010-05-27 | シュ サント−ジュスティーヌ | 骨吸収と骨形成の不均衡を是正するための方法ならびにキット及び組成物 |
Families Citing this family (61)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6638963B1 (en) * | 1990-12-04 | 2003-10-28 | Oregon Health And Science University | Methods for treating circadian rhythm disorders |
| US5637770A (en) * | 1991-01-16 | 1997-06-10 | Daiichi Pharmaceutical Co., Ltd. | Hexa-cyclic compound |
| GB9114947D0 (en) * | 1991-07-11 | 1991-08-28 | Pfizer Ltd | Process for preparing sertraline |
| AU660336B2 (en) * | 1991-10-18 | 1995-06-22 | Alza Corporation | Device for the transdermal administration of melatonin |
| US5416118A (en) * | 1992-04-09 | 1995-05-16 | Schering Corporation | Bicyclic amides as inhibitors of acyl-coenzyme A: cholesterol acyl transferase |
| WO1994022495A1 (fr) * | 1993-03-31 | 1994-10-13 | The Trustees Of The University Of Pennsylvania | Ligands de recepteurs de la dopamine d-3 et de la serotonine (5-ht1a) et agents d'imagerie |
| US5914349A (en) * | 1994-01-10 | 1999-06-22 | Teva Pharmaceutical Industries, Ltd. | Compositions containing and methods of using 1-aminoindan and derivatives thereof and process for preparing optically active 1-aminoindan derivatives |
| WO1995030644A1 (fr) * | 1994-05-10 | 1995-11-16 | The Wellcome Foundation Limited | Derives amides et leur utilisation therapeutique |
| WO1996008466A1 (fr) * | 1994-09-12 | 1996-03-21 | Takeda Chemical Industries, Ltd. | Composes benzocycloalcenes, leur production et leur utilisation |
| US5541228A (en) * | 1994-10-14 | 1996-07-30 | Bristol-Myers Squibb Co. | Melatonergic agents |
| US5530012A (en) * | 1994-12-22 | 1996-06-25 | Bristol-Myers Squibb Co. | 3-alkoxybenzylpiperidine derivatives as melatonergic agents |
| AU4569496A (en) * | 1995-02-24 | 1996-09-05 | Bristol-Myers Squibb Company | Tetralinyl- and indanyl-ethylamides |
| US5661186A (en) * | 1995-02-24 | 1997-08-26 | Bristol-Myers Squibb Co. | Tetralinyl-and indanyl-ethylamides |
| FR2732964B1 (fr) * | 1995-04-14 | 1997-05-16 | Adir | Nouveaux amides tricycliques, leurs procedes de preparation et les compositions pharmaceutiques qui les contiennent |
| FR2734814B1 (fr) * | 1995-05-31 | 1997-07-04 | Adir | Nouveaux composes alkoxy-aryles, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| US5596019A (en) * | 1995-06-07 | 1997-01-21 | Bristol-Myers Squibb Company | N-acyl-cycloalkylamine derivatives as melatonergics |
| CA2176854A1 (fr) * | 1995-06-07 | 1996-12-08 | Daniel J. Keavy | Derives de n-acyl-2-arylcyclopropylmethylamine, agents melatonergiques |
| DE69616357T2 (de) * | 1995-07-26 | 2002-07-11 | Takeda Chemical Industries, Ltd. | Benzocycloalken-verbindungen mit bindungsaffinität an den melatonin-rezeptor, ihre herstellung und verwendung |
| US6034239A (en) * | 1996-03-08 | 2000-03-07 | Takeda Chemical Industries, Ltd. | Tricyclic compounds, their production and use |
| US5808151A (en) * | 1996-04-17 | 1998-09-15 | Bristol-Myers Squibb Company | Biphenylamido derivatives as melatonergic agents |
| US6310085B1 (en) * | 1997-10-03 | 2001-10-30 | Clarencew Pty Ltd. | Method for the treatment of neurological or neuropsychiatric disorders |
| ZA9711051B (en) * | 1996-12-10 | 1999-06-09 | Bristol Myers Squibb Co | Benzodioxole benzofuran dihydrobenzofuran and benzodioxane melatonergic agents |
| PT966435E (pt) | 1996-12-18 | 2005-06-30 | Yissum Res Dev Co | Derivados aminoindano |
| US6028112A (en) * | 1997-05-23 | 2000-02-22 | Bristol-Myers Squibb Company | Spirocyclopropyl fluorenes as melatonergic agents |
| WO1999048859A1 (fr) * | 1998-03-20 | 1999-09-30 | Bristol-Myers Squibb Company | Aryloxyanilides et composes associes |
| CA2334299A1 (fr) | 1998-06-05 | 1999-12-09 | Pierre Dextraze | Melatonergiques a base de derives cis heterocycliques de cyclopropane |
| US6022980A (en) * | 1998-07-16 | 2000-02-08 | Eli Lilly And Company | Preparation of 4-halo and 6-halomelatonins |
| US6737547B1 (en) | 1998-12-31 | 2004-05-18 | Teva Pharmaceutical Industries, Ltd. | Compositions containing and methods of using N-acyl-1H-aminoindenes |
| US6664293B2 (en) * | 1999-02-26 | 2003-12-16 | Fujiwawa Pharmaceutical Co., Ltd. | Amide compounds for the potentiation of cholinergic activity |
| EP1189900B1 (fr) | 1999-06-30 | 2004-01-14 | Bristol-Myers Squibb Company | Derives d'aminopyrrolidine heterocycliques utilises en tant qu'agents melatonergiques |
| CA2382418A1 (fr) | 1999-08-20 | 2001-03-01 | Shigenori Ohkawa | Derives de dihydrobenzofuran, leur procede de preparation et agents |
| CA2381860C (fr) | 1999-08-26 | 2009-11-24 | Takeda Chemical Industries, Ltd. | Matrice adherant a la muqueuse nasale |
| DE10041478A1 (de) | 2000-08-24 | 2002-03-14 | Sanol Arznei Schwarz Gmbh | Neue pharmazeutische Zusammensetzung |
| PE20020856A1 (es) * | 2001-02-13 | 2002-11-11 | Aventis Pharma Gmbh | 1,2,3,4-tetrahidronaftil aminas aciladas |
| US20040010038A1 (en) * | 2002-02-27 | 2004-01-15 | Eran Blaugrund | Propargylamino indan derivatives and propargylamino tetralin derivatives as brain-selective MAO inhibitors |
| EP1426049B1 (fr) * | 2002-12-02 | 2005-05-18 | Schwarz Pharma Ag | Administration par iontophorèse de rotigotine pour traiter la maladie de Parkinson |
| DE10334187A1 (de) * | 2003-07-26 | 2005-03-03 | Schwarz Pharma Ag | Substituierte 2-Aminotetraline zur Behandlung von Depressionen |
| DE10334188B4 (de) * | 2003-07-26 | 2007-07-05 | Schwarz Pharma Ag | Verwendung von Rotigotin zur Behandlung von Depressionen |
| DE10361258A1 (de) * | 2003-12-24 | 2005-07-28 | Schwarz Pharma Ag | Verwendung von substituierten 2-Aminotetralinen zur vorbeugenden Behandlung von Morbus Parkinson |
| US20050197385A1 (en) * | 2004-02-20 | 2005-09-08 | Schwarz Pharma Ag | Use of rotigotine for treatment or prevention of dopaminergic neuron loss |
| DE102004014841B4 (de) * | 2004-03-24 | 2006-07-06 | Schwarz Pharma Ag | Verwendung von Rotigotin zur Behandlung und Prävention des Parkinson-Plus-Syndroms |
| EP1956904B1 (fr) * | 2005-12-09 | 2017-04-12 | Yissum Research Development Company of the Hebrew University of Jerusalem Ltd. | Ladostigil a faible dose pour le traitement du déficit cognitif léger |
| TW200744576A (en) * | 2006-02-24 | 2007-12-16 | Teva Pharma | Propargylated aminoindans, processes for preparation, and uses thereof |
| CA2651862A1 (fr) * | 2006-05-09 | 2007-11-22 | Braincells, Inc. | Neurogenese induite par le recepteur 5ht |
| EA017836B1 (ru) | 2007-11-28 | 2013-03-29 | ЮСиБи ФАРМА ГМБХ | Новая полиморфная форма ротиготина и способ ее получения |
| MX2010010773A (es) | 2008-04-01 | 2011-04-11 | Abbott Gmbh & Co Kg | Tetrahidroisoquinolinas, composiciones farmaceuticas que las contienen y su uso en terapia. |
| AR075442A1 (es) | 2009-02-16 | 2011-03-30 | Abbott Gmbh & Co Kg | Derivados de aminotetralina, composiciones farmaceuticas que las contienen y sus usos en terapia |
| US9051280B2 (en) | 2010-08-13 | 2015-06-09 | AbbVie Deutschland GmbH & Co. KG | Tetraline and indane derivatives, pharmaceutical compositions containing them, and their use in therapy |
| US8883839B2 (en) | 2010-08-13 | 2014-11-11 | Abbott Laboratories | Tetraline and indane derivatives, pharmaceutical compositions containing them, and their use in therapy |
| US8846743B2 (en) | 2010-08-13 | 2014-09-30 | Abbott Laboratories | Aminoindane derivatives, pharmaceutical compositions containing them, and their use in therapy |
| US8877794B2 (en) | 2010-08-13 | 2014-11-04 | Abbott Laboratories | Phenalkylamine derivatives, pharmaceutical compositions containing them, and their use in therapy |
| US9045459B2 (en) | 2010-08-13 | 2015-06-02 | AbbVie Deutschland GmbH & Co. KG | Phenalkylamine derivatives, pharmaceutical compositions containing them, and their use in therapy |
| US9309200B2 (en) | 2011-05-12 | 2016-04-12 | AbbVie Deutschland GmbH & Co. KG | Benzazepine derivatives, pharmaceutical compositions containing them, and their use in therapy |
| US8853196B2 (en) | 2011-08-05 | 2014-10-07 | AbbVie Deutschland GmbH & Co. KG | Aminochromane, aminothiochromane and amino-1,2,3,4-tetrahydroquinoline derivatives, pharmaceutical compositions containing them, and their use in therapy |
| MX2014006004A (es) | 2011-11-18 | 2015-04-16 | Abbvie Deutschland | Derivados de aminobenzociclohepteno, aminotetralina, aminoindano y fenalcilamina n-sustituidas, composiciones farmaceuticas que los contienen, y su uso en terapia. |
| US9365512B2 (en) | 2012-02-13 | 2016-06-14 | AbbVie Deutschland GmbH & Co. KG | Isoindoline derivatives, pharmaceutical compositions containing them, and their use in therapy |
| EP2909166A4 (fr) * | 2012-10-22 | 2016-10-26 | Symed Labs Ltd | Procédé pour la préparation d'agomélatine à l'aide de nouveaux intermédiaires |
| US9656955B2 (en) | 2013-03-15 | 2017-05-23 | Abbvie Inc. | Pyrrolidine derivatives, pharmaceutical compositions containing them, and their use in therapy |
| US9650334B2 (en) | 2013-03-15 | 2017-05-16 | Abbvie Inc. | Pyrrolidine derivatives, pharmaceutical compositions containing them, and their use in therapy |
| EP3057960B1 (fr) | 2013-10-17 | 2019-02-27 | AbbVie Deutschland GmbH & Co. KG | Dérivés d'aminochromane, d'aminothiochromane et d'amino-1,2,3,4-tétrahydroquinoléine, compositions pharmaceutiques contenant ceux-ci et leur utilisation thérapeutique |
| MX2016004934A (es) | 2013-10-17 | 2016-12-20 | Abbvie Deutschland | Derivados de aminotetralina y aminoindano, composiciones farmaceuticas que los contienen, y su uso en terapia. |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2022746A1 (de) * | 1970-05-09 | 1971-12-02 | Bochringer Mannheim Gmbh | Blutzuckersenkende Sulfonylaminopyrimidine und Verfahren zu deren Herstellung |
| US4107206A (en) * | 1974-04-08 | 1978-08-15 | Akzona Incorporated | Benzo-bicyclononene- derivatives |
| DK254975A (da) * | 1974-06-12 | 1975-12-13 | Takeda Chemical Industries Ltd | Fremgangsmade til fremstilling af aminotetralolforbindelser |
| US4049717A (en) * | 1976-05-13 | 1977-09-20 | American Cyanamid Company | Novel 1,2,3,4-tetrahydro-4-oxo-(oxy)-1-naphthylamines and method of preparation thereof |
| JPS6045180B2 (ja) * | 1977-05-17 | 1985-10-08 | 第一製薬株式会社 | ２−アミノテトラリン誘導体 |
| US4254268A (en) * | 1977-09-16 | 1981-03-03 | American Cyanamid Company | Process for preparation 4,5,6,7-tetrahydro-7-oxobenzo-[b]-thiophenes and 1,2,3,4-tetrahydro-4-oxo-1-naphthalenes |
| CH637363A5 (en) * | 1977-11-24 | 1983-07-29 | Sandoz Ag | Process for preparing novel 2-aminotetralins |
| US4320148A (en) * | 1980-11-24 | 1982-03-16 | Smithkline Corporation | 2-Aminotetralin compounds, pharmaceutical compositions and method of producing central alpha1 agonist activity |
| FR2512814A1 (fr) * | 1981-09-16 | 1983-03-18 | Synthelabo | Derives d'amino-2 tetrahydro-1,2,3,4 naphtalene, leur preparation et leur application en therapeutique |
| NL194166C (nl) * | 1984-06-12 | 2001-08-03 | Novartis Ag | Naftoxazinen en bereiding en toepassing daarvan. Hexahydronaft[2,3-b]-1,4-oxazinen en farmaceutische preparaten die ze bevatten. |
| DE3623941A1 (de) * | 1986-07-16 | 1988-01-28 | Bayer Ag | Substituierte amino-5,6,7,8-tetrahydronaphthyl-oxyessigsaeuren, verfahren zu deren herstellung sowie die verwendung als arzneimittel |
| FR2613365B1 (fr) * | 1987-04-01 | 1989-07-28 | Adir | Nouveaux derives de l'amino tetrahydro-5, 6, 7, 8 naphto (2, 3b) furanne, leurs procedes de preparation et les compositions pharmaceutiques qui les contiennent |
| FI900801A7 (fi) * | 1987-08-17 | 1990-02-16 | Nelson Res & Development Co | Melantoniinianalogit |
| CA1331191C (fr) * | 1988-03-25 | 1994-08-02 | Bengt Ronny Andersson | Derives de la tetraline utiles comme medicaments |
| EP0381902A1 (fr) * | 1989-01-09 | 1990-08-16 | Merrell Dow Pharmaceuticals Inc. | Dérivés de tétraline |
-
1989
- 1989-09-25 US US07/411,675 patent/US5071875A/en not_active Expired - Lifetime
-
1990
- 1990-09-21 CA CA002025958A patent/CA2025958A1/fr not_active Abandoned
- 1990-09-21 EP EP19900118198 patent/EP0420064A3/en not_active Withdrawn
- 1990-09-24 IE IE343090A patent/IE903430A1/en unknown
- 1990-09-24 AU AU63111/90A patent/AU642429B2/en not_active Ceased
- 1990-09-24 ZA ZA907597A patent/ZA907597B/xx unknown
- 1990-09-25 KR KR1019900015228A patent/KR910006218A/ko not_active Withdrawn
- 1990-09-25 JP JP2254980A patent/JPH03169840A/ja active Pending
- 1990-09-25 PT PT95417A patent/PT95417A/pt not_active Application Discontinuation
-
1993
- 1993-07-28 AU AU44222/93A patent/AU4422293A/en not_active Abandoned
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2008518003A (ja) * | 2004-10-29 | 2008-05-29 | アストラゼネカ・アクチエボラーグ | 医薬品としての不飽和キノリンもしくはナフタレン誘導体の使用 |
| JP2009527462A (ja) * | 2006-01-06 | 2009-07-30 | セプラコア インコーポレーテッド | テトラロン系モノアミン再取り込み阻害剤 |
| JP2010518129A (ja) * | 2007-02-15 | 2010-05-27 | シュ サント−ジュスティーヌ | 骨吸収と骨形成の不均衡を是正するための方法ならびにキット及び組成物 |
Also Published As
| Publication number | Publication date |
|---|---|
| CA2025958A1 (fr) | 1991-03-26 |
| AU6311190A (en) | 1991-03-28 |
| KR910006218A (ko) | 1991-04-27 |
| PT95417A (pt) | 1991-05-22 |
| US5071875A (en) | 1991-12-10 |
| EP0420064A3 (en) | 1992-02-26 |
| AU4422293A (en) | 1993-10-14 |
| AU642429B2 (en) | 1993-10-21 |
| ZA907597B (en) | 1991-07-31 |
| EP0420064A2 (fr) | 1991-04-03 |
| IE903430A1 (en) | 1991-04-10 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JPH03169840A (ja) | メラトニン作用物質及び拮抗物質としての置換２‐アミドテトラリン | |
| US5151446A (en) | Substituted 2-amidotetralins as melatonin agonists and antagonists | |
| Morgan et al. | Central melatonin receptors: implications for a mode of action | |
| Neubert et al. | Down-regulation of adhesion receptors on cells of primate embryos as a probable mechanism of the teratogenic action of thalidomide | |
| Drukarch et al. | D-2 dopamine autoreceptor selective drugs: do they really exist? | |
| RO120134B1 (ro) | Trihidrat de metansulfonat de (1s, 2s)-1-(4-hidroxifenil)-2-(4-hidroxi-4-fenilpiperidin-1-il)-1-propanol şi compoziţie farmaceutică | |
| JP2004002437A (ja) | 神経障害および神経病の治療に有用な受容体作動性カルシウムチャネル上の新規部位で活性な化合物 | |
| JPH06510531A (ja) | カルシウム受容体活性化分子 | |
| LT3530B (en) | Process for preparation of phenyl alkylamines | |
| JPH08503208A (ja) | 新規な３，３−ジフェニルプロピルアミン類、その使用および製造法 | |
| JPH06501002A (ja) | シグマ受容体に対して高い結合性を有する置換アミジン類およびその使用 | |
| CA2337822A1 (fr) | Inhibiteurs de vehicule d'anandamide comme agents analgesiques | |
| DE69828508T2 (de) | Tropananloga und methoden zur hemmung des transportes von monoaminen | |
| Molewijk et al. | Reduction of guinea pig pup isolation calls by anxiolytic and antidepressant drugs | |
| Pujol et al. | First appearance and development of motile properties in outer hair cells isolated from guinea-pig cochlea | |
| Mathe-Allainmat et al. | Synthesis of 2-amido-2, 3-dihydro-1 H-phenalene derivatives as new conformationally restricted ligands for melatonin receptors | |
| US5639751A (en) | N-acyl-2,3-benzodiazepine derivatives for treating acute and chronic neurodegenerative disorders | |
| Cannon et al. | Comparison of biological effects of N-alkylated congeners of. beta.-phenethylamine derived from 2-aminotetralin, 2-aminoindan, and 6-aminobenzocycloheptene | |
| JPH08506357A (ja) | ５−ｈｔ１ｄ選択性を有するトリプトアミン類似体 | |
| Guerrero et al. | Nocturnal decreases in nitric oxide and cyclic GMP contents in the chick brain and their prevention by light | |
| Lauterbach | Reversible intermittent rhythmic myoclonus with fluoxetine in presumed Pick's disease | |
| EA012283B1 (ru) | Новые соединения нафталина, способ их получения и фармацевтические композиции, содержащие их | |
| US4053632A (en) | Compounds of spiro-amine type and methods for their use | |
| EP0709371B1 (fr) | O-arylméthyl N-(thio)acyl hydroxylamines comme ligands des récepteurs de la mélatonine, leurs procédés de préparation et les compositions pharmaceutiques qui les contiennent | |
| CA2849309A1 (fr) | Nouveaux composes modulateurs de la voie de signalisation des proteines hedgehog, leurs formes marquees, et applications |